Isobutyl chloroformate → 4-Hydroxybiphenyl

HRID 1439198Notes

Reaction equation

HRID 1439198 reaction equation
CCCCC[C@H](O)/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19]CC(O)=O)[C:12](=[O:13])[CH:11]=[CH:10]1.C(OC(Cl)=O)C(C)C>C(N(CC)CC)C>[C:14]1([C:9]2[CH:8]=[CH:7][C:12]([OH:13])=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 5280880(+)-Prostaglandin A2

Product 1

HCID 71034-Hydroxybiphenyl

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1 but using 0.561 g. of PGA2, 0.302 ml. of triethylamine, 0.286 ml. of isobutylchloroformate, and 0.570 g. of p-phenylphenol, there is obtained a crude oily residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate-hexane (2:3) saturated with water. The residue obtained by concentration of selected fractions, 0.381 g., an oil, is the title compound, having Rf 0.5 (TLC on silica gel in ethyl acetate-hexane (2:3).

Sources & evidence

ORD record
ord-7234a5f182044326aae75f94a14bf511
Source dataset
uspto-grants-1977_11
Patent number
US04058551

Reaction notes

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